Main Article Content

Abstract

The lemon juice anchored polyaniline nanoparticles were synthesized using aniline as a monomer and lemon juice as acid dopant with potassium persulfate as the oxidant. The synthesized nanoparticles were characterized by XRD, FESEM and EDX. The XRD pattern of polyaniline-lemon juice has been shown crystalline nature and the average size found to be 2.998 nm. The polyaniline-lemon juice nanoparticles were immobilized on column silica by grinding method. The polyaniline-lemon juice@silica nanocomposite were characterized by XRD and FESEM. The XRD pattern of polyaniline-lemon juice@silica nanocomposite has been shown amphorous nature. This study has explored the catalytic application of these nanocomposites in the synthesis of various β-amino ketones via a one-pot three-component Mannich reaction of aldehydes, ketones and aromatic amines. This method provides a novel and enhanced amendment of three-component Mannich reaction in terms of mild reaction conditions and clean reaction profiles, using a small quantity of catalyst and simple workup procedure.

Keywords

Polyaniline Multicomponent reaction Mannich reaction Lemon juice Nanocomposite Silica.

Article Details

How to Cite
Kulkarni, P., & Kohinkar, S. (2021). Polyaniline-Lemon Juice@Silica Nanocomposities an Efficient Catalyst for Synthesis of β-Amino Ketone. Asian Journal of Organic & Medicinal Chemistry, 6(1), 59–67. https://doi.org/10.14233/ajomc.2021.AJOMC-P308

References

  1. A. Dömling and I. Ugi, Multicomponent Reactions with Isocyanides, Angew. Chem. Int. Ed., 39, 3168 (2000); https://doi.org/10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
  2. J. Zhu and H. Bienaymé Multicomponent Reactions, Wiley-VCH: Weinheim, Germany, p. 76 (2005).
  3. H.C. Kolb, M.G. Finn and K.B. Sharpless, Click Chemistry: Diverse Chemical Function from a Few Good Reactions, Angew. Chem. Int. Ed., 40, 2004 (2001); https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
  4. S. Kobayashi and H. Ishitani, Catalytic Enantioselective Addition to Imines, Chem. Rev., 99, 1069 (1999); https://doi.org/10.1021/cr980414z
  5. F.A. Davis, Y. Zhang and G. Anilkumar, Asymmetric Synthesis of the Quinolizidine Alkaloid (-)-Epimyrtine with Intramolecular Mannich Cyclization and N-Sulfinyl d-Amino b-Ketoesters, J. Org. Chem., 68, 8061 (2003); https://doi.org/10.1021/jo030208d
  6. J. Barluenga, A.L. Viado, E. Aguilar, S. Fustero and B. Olano, 1,3-Amino alcohols from 4-Amino-1-azadienes. Diastereo- and Enantioselective Approach to the Four Diastereoisomers of the N-Terminal Amino Acid Component of Nikkomycins B and BX, J. Org. Chem., 58, 5972 (1993); https://doi.org/10.1021/jo00074a024
  7. S.S. Mansoor, K. Aswin, K. Logaiya and S.P.N. Sudhan, An Efficient Synthesis of b-Amino Ketone Compounds through One-Pot Three-Component Mannich-Type Reactions using Bismuth Nitrate as Catalyst, J. Saudi Chem. Soc., 19, 379 (2015); https://doi.org/10.1016/j.jscs.2012.04.008
  8. R. Quevedo and B. Moreno-Murillo, One-Step Synthesis of a New Heterocyclophane Family, Tetrahedron Lett., 50, 936 (2009); https://doi.org/10.1016/j.tetlet.2008.12.023
  9. G. Rossino, M. Raimondi, M. Rui, M. Di Giacomo, D. Rossi and S. Collina, PEG 400/Cerium Ammonium Nitrate Combined with Micro-wave-Assisted Synthesis for Rapid Access to b-Amino Ketones. An Easy-to-Use Protocol for Discovering New Hit Compounds, Molecules, 23, 775 (2018); https://doi.org/10.3390/molecules23040775
  10. H. Lu, Z. Luo, R. Wu, H. Cheng, S. Nie, Y. Tang and Y. Gao, An Efficient, Mild, Solvent-Free, One-Pot Three-Component Mannich Reaction Catalyzed by (C4H12N2)2[BiCl6]Cl·H2O, Synthesis, 47, 1447 (2015); https://doi.org/10.1055/s-0034-1380278
  11. Q. Guo and J.C.-G. Zhao, Highly Enantioselective Three-Component Direct Mannich Reactions of Unfunctionalized Ketones Catalyzed by Bifunctional Organocatalysts, Org. Lett., 15, 508 (2013); https://doi.org/10.1021/ol303315c
  12. N.S. Josephsohn, M.L. Snapper and A.H. Hoveyda, Ag-Catalyzed Asymmetric Mannich Reactions of Enol Ethers with Aryl, Alkyl, Alkenyl, and Alkynyl Imines, J. Am. Chem. Soc., 126, 3734 (2004); https://doi.org/10.1021/ja049388e
  13. Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji and K. Sakai, The Direct and Enantioselective, One-Pot, Three-Component, Cross-Mannich Reaction of Aldehydes, Angew. Chem. Int. Ed., 42, 3677 (2003); https://doi.org/10.1002/anie.200351813
  14. J. Jiang, H.-D. Xu, J.-B. Xi, B.-Y. Ren, F.-P. Lv, X. Guo, L.-Q. Jiang, Z.-Y. Zhang and W.-H. Hu, Diastereoselectively Switchable Enantio-selective Trapping of Carbamate Ammonium Ylides with Imines, J. Am. Chem. Soc., 133, 8428 (2011); https://doi.org/10.1021/ja201589k
  15. M.M. Salter, J. Kobayashi, Y. Shimizu and S. Kobayashi, Direct-Type Catalytic Three-Component Mannich Reactions Leading to an Efficient Synthesis of a,ß-Diamino Acid Derivatives, Org. Lett., 8, 3533 (2006); https://doi.org/10.1021/ol0613012
  16. B. Eftekhari-Sis, A. Abdollahifar, M.M. Hashemi and M. Zirak, Stereo-selective Synthesis of b-Amino Ketones via Direct Mannich-Type Reactions, Catalyzed with ZrOCl2·8H2O under Solvent-Free Conditions, Eur. J. Org. Chem., 2006, 5152 (2006); https://doi.org/10.1002/ejoc.200600493
  17. Y. Tanaka, T. Hasui and M. Suginome, Diarylborinic Acid Derivatives as a Catalytic Iminium Ion Generator in the Mannich-type Reaction Using sec-Amines, Aldehydes, and Ketene Silyl Acetals, Synlett, 1239 (2008); https://doi.org/10.1055/s-2008-1072724
  18. M. Hatano, T. Maki, K. Moriyama, M. Arinobe and K. Ishihara, Pyridinium 1,1¢-Binaphthyl-2,2¢-disulfonates as Highly Effective Chiral Brønsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction, J. Am. Chem. Soc., 130, 16858 (2008); https://doi.org/10.1021/ja806875c
  19. M. Hatano, T. Horibe and K. Ishihara, Chiral Lithium(I) Binaphtholate Salts for the Enantioselective Direct Mannich-Type Reaction with a Change of Syn/Anti and Absolute Stereochemistry, J. Am. Chem. Soc., 132, 56 (2010); https://doi.org/10.1021/ja909874b
  20. H.A. Patel, A.L. Patel and A.V. Bedekar, Polyaniline Coated on Celite, a Heterogeneous Support for Palladium: Applications in Catalytic Suzuki and One-pot Suzuki-Aldol Reactions, New J. Chem., 40, 8935 (2016); https://doi.org/10.1039/C6NJ02402E
  21. E. Blaz and J. Pielichowski, Polymer-Supported Cobalt (II) Catalysts for the Oxidation of Alkenes, Molecules, 11, 115 (2006); https://doi.org/10.3390/11010115
  22. A.A. Yelwande, B.R. Arbad and M.K. Lande, Polyaniline/SiO2 Catalyzed One-pot Mannich Reaction: An Efficient Synthesis of b-amino Carbonyl Compounds, J. Korean Chem. Soc., 55, 644 (2011); https://doi.org/10.5012/jkcs.2011.55.4.644
  23. V. Gautam, K.P. Singh and V.L. Yadav, Multicomponent Template Effects-Preparation of Highly Porous Polyaniline Nanorods Using Crude Lemon Juice and Its Application for Selective Detection of Catechol, ACS Sustain. Chem.& Eng., 6, 2256 (2018); https://doi.org/10.1021/acssuschemeng.7b03705
  24. M.O.H. Helali, M. Ibrahim, M.Z. Shafique, M.M. Rahman, S.K. Biswas and M.S. Islam, Formulation, Preparation and Preservation of Lemon (Citrus limon L.) Cordial, J. Biosci., 16, 125 (1970); https://doi.org/10.3329/jbs.v16i0.3755
  25. N.A.R. Deshpande, S.P. Somani, S.D. Chakane, P.G. Saptarshi and P.R. Somani, Environment-Friendly Synthesis of Nano-Structured Conducting Polyaniline Using Lemon Juice, J. Green Sci. Technol., 1, 127 (2013); https://doi.org/10.1166/jgst.2013.1020
  26. P. Kulkarni, B. Totawar and P. Zubaidha, An Efficient Synthesis of b-Aminoketone Compounds through Three-Component Mannich Reaction Catalyzed by Calcium Chloride, Monatsh. Chem., 143, 625 (2012); https://doi.org/10.1007/s00706-011-0609-0
  27. Z. Li, X. Ma, J. Liu, X. Feng, G. Tian and A. Zhu, Silica-Supported Aluminum Chloride: A Recyclable and Reusable Catalyst for One-Pot Three-Component Mannich-Type Reactions, J. Mol. Catal. Chem., 272, 132 (2007); https://doi.org/10.1016/j.molcata.2007.03.029
  28. H. Li, H.-y. Zeng and H. Shao, Bismuth(III) Chloride-catalyzed One-Pot Mannich Reaction: Three-component Synthesis of b-Amino Carbonyl Compounds, Tetrahedron Lett., 50, 6858 (2009); https://doi.org/10.1016/j.tetlet.2009.09.131
  29. F. Kabiri Esfahani, D. Zareyee, A. Shokuhi Rad and S. Taher-Bahrami, Sulfonic Acid Supported on Magnetic Nanoparticle as an Eco-friendly, Durable and Robust Catalyst for the Synthesis of b-Amino Carbonyl Compounds through Solvent Free Mannich Reaction, Appl. Organomet. Chem., 31, e3865 (2017); https://doi.org/10.1002/aoc.3865
  30. S. Ramalingam and P. Kumar, Multi-Component Carbon-Carbon Bond forming Mannich Reaction Catalyzed by Yttria-Zirconia based Lewis Acid, Catal. Commun., 9, 2445 (2008); https://doi.org/10.1016/j.catcom.2008.06.011